cis-trans Enantiomerism in the Diels-Alder cycloadducts of 6-arylfulvenes with maleic anhydride:resolution of the exo adducts via the N-((1S)-1-(naphth-1-yl)ethyl)imide derivatives:assignment of the absoluteconfigurations based on the crystal structure of an imide diastereomer

Chandrasekhar, S and Gorla, SK (2006) cis-trans Enantiomerism in the Diels-Alder cycloadducts of 6-arylfulvenes with maleic anhydride:resolution of the exo adducts via the N-((1S)-1-(naphth-1-yl)ethyl)imide derivatives:assignment of the absoluteconfigurations based on the crystal structure of an imide diastereomer. In: Tetrahedron-Asymmetry, 17 (1). pp. 92-98.

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Abstract

A new case of the uncommon cis-trans enantiomerism is presented. The titled anhydride adducts were prepared in good yields by the known reaction of three 6-arylfulvenes with maleic anhydride (aryl = phenyl, p-tolyl and p-anisyl). The exo adducts were converted to the corresponding imides by reaction with (1S)-1-(naphth-1-yl)ethylamine in similar to 80% yields, and the resulting diastereomeric imides separated by silica gel column chromatography. They were hydrolysed and recyclised to the chiral anhydrides, in 'one-pot' with 10% NaOH-EtOH, followed by treatment with 2 M HCl, in similar to 40% yields. The titled anhydrides were thus obtained in homochiral form, in enantiomeric purities (generally) of similar to 90% as indicated by chiral HPLC. The chiral anhydrides were also converted to the corresponding imides (presumably stereospecifically), by treatment with ammonia solution in excellent yields. The crystal structure of one of the above diastereomeric imides (derived from 6-phenylfulvene) was determined, and based on the known (S)-configuration of the naphthylethylamine moiety, the 'configurations' of the original anhydride adducts were assigned

Item Type:	Journal Article
Publication:	Tetrahedron-Asymmetry
Publisher:	Elsavier
Additional Information:	Copyright of this article belongs to Elsavier
Keywords:	Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical;Acid
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	26 Dec 2008 11:17
Last Modified:	19 Sep 2010 04:54
URI:	http://eprints.iisc.ac.in/id/eprint/16962

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